Town of Windham, New York Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Town of Windham, New York on RentalSaver.com!

Town of Windham Rentals

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From $199 per night (USD)
VRBO
Windham Home Near Mountain Biking & Hiking Trails!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
This 2-bed, 2-bath vacation rental in Windham is perfect for a small group of friends or family looking to unplug, unwin ...
From $199 per night (USD)
VRBO
From $254 per night (USD)
Expedia
Newly Renovated Ski House in Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to our charming and cozy retreat in the heart of Windham, where modern comfort meets historic charm. With its pr ...
From $254 per night (USD)
Expedia
From $343 per night (USD)
VRBO
5 Min to Skiing | Hot Tub | Fire Pit | Pool Table
Bedrooms:
2
Bathrooms:
3
Sleeps:
10
Escape to this newly renovated mountain cabin just 5 minutes from Windham Mountain ski resort! With a private fishing po ...
From $343 per night (USD)
VRBO
From $331 per night (USD)
VRBO
Jewett's Gem: a comfortable, cozy, and stylish mountain getaway in the Catskills
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Jewett’s Gem is a cozy two bedroom condo situated between Hunter and Windham Mountains in the heart of the Catskills. F ...
From $331 per night (USD)
VRBO
From $1105 per night (USD)
VRBO
Brand New Luxury Ski Cabin - 2 Mi to Windham Mtn!
Bedrooms:
5
Bathrooms:
6
Sleeps:
12
Witness the breathtaking beauty of the Catskill Mountains at this stunning 6-bed, 5.5-bath vacation rental. Nestled in n ...
From $1105 per night (USD)
VRBO
From $817 per night (USD)
Expedia
Luxury Ski-in Ski-Out 4 Bedroom 10 Bed Condo at Whisper Creek Windham Mountain
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Ski-In / Ski-Out Luxury 4 bedroom, 4 bath, condo at the base of Windham Mountain! Owned and designed primarily for pers ...
From $817 per night (USD)
Expedia
From $1065 per night (USD)
VRBO
Bump Mountain Retreat: Hot Tub, Sauna, Pool, Game Room, Piano & Panoramic Views
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
If you're looking for a luxurious ski retreat a short drive from NYC, then look no further. Perched on a mountainside, B ...
From $1065 per night (USD)
VRBO
Click For Pricing
Expedia
Windham House with Hot Tub perfect for families
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Spacious restored family house just, 1.7 miles from Ski Windham and 6.7 miles from Hunter Mountain. Three large family r ...
Click For Pricing
Expedia
From $239 per night (USD)
VRBO
A cozy place to recharge in the Catskills Mountains Summer Paradise
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
A serene Catskills 2-bedroom condo, 10 minutes to Hunter and Windham mountain ski resorts. Ideal for ski enthusiasts, it ...
From $239 per night (USD)
VRBO
From $567 per night (USD)
VRBO
Luxury Ski-in Ski-Out Condo + Amenities
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Please message me for long term and/or seasonal rental inquiries. This Whisper Creek condo is located in the newest lux ...
From $567 per night (USD)
VRBO
From $471 per night (USD)
VRBO
Luxurious 3BR/2BA Chalet w/ Panoramic Views Near Windham Mountain on 22+ Acres
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Winter is here and our chalet offers the perfect balance of privacy and proximity to Windham. Be advised that a vehicl ...
From $471 per night (USD)
VRBO
From $1901 per night (USD)
VRBO
Windham ski in-out condo, luxury 2000+ sf modern 5BR, hot tub, pool, boot room++
Bedrooms:
4
Bathrooms:
5
Sleeps:
12
We are renting our 2000+ sf modern, renovated, mountain facing luxury condo at Whisper Creek to someone who will take gr ...
From $1901 per night (USD)
VRBO
From $245 per night (USD)
VRBO
Vacation Rental Home ~ 2 Mi to Windham Mountain!
Bedrooms:
1
Bathrooms:
3
Sleeps:
9
Discover the charming town of Windham, NY, and stay at this spacious 3-bedroom, 1.5-bath vacation rental. With a cozy fi ...
From $245 per night (USD)
VRBO
From $1665 per night (USD)
VRBO
Lux Mansion Windham, Catskills Hot Tub, BBQ, Pool Table, Fire pit, Pond
Bedrooms:
5
Bathrooms:
6
Sleeps:
16
SPECIAL OFFER until the end of December! Book 2 nights on weekdays and get 50% off the 3rd night (weekdays only) We ...
From $1665 per night (USD)
VRBO
Click For Pricing
VRBO
Catskill Mountain Ski House
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Cozy 2 bedroom condo two minutes from Windham Mountain. Your family will be close to everything when you stay at this ce ...
Click For Pricing
VRBO
From $481 per night (USD)
Expedia
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
Bedrooms:
3
Bathrooms:
9
Sleeps:
25
Step into the heartwarming embrace of history at our enchanting 1800's residence! This cherished abode beckons you with ...
From $481 per night (USD)
Expedia
From $1061 per night (USD)
VRBO
Lux Windham Getaway | Views & Indoor Heated Pool
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Summary: Welcome to your luxury mountain retreat — the perfect blend of high-end comfort and alpine charm. Perched to ca ...
From $1061 per night (USD)
VRBO
From $589 per night (USD)
VRBO
Beautiful Catskills country retreat --neighboring reservoir/recreation area
Bedrooms:
2
Bathrooms:
5
Sleeps:
12
The dancing bear welcomes you to our beautiful, fully restored, 1800’s farmhouse on 5 acres of woods and a large grass y ...
From $589 per night (USD)
VRBO
From $1245 per night (USD)
VRBO
Custom Windham Mtn Villa w/ Pool, Theater & Views!
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
The poster child for a 'dream house,' this stunning 5-bedroom, 4.5-bath vacation rental is sure to be adored by luxury t ...
From $1245 per night (USD)
VRBO
From $3429 per night (USD)
VRBO
Luxurious ski in/out, 3-story chalet directly on the slopes of Windham Mountain
Bedrooms:
7
Bathrooms:
7
Sleeps:
12
Luxurious ski in/ ski out, three-story chalet located directly on the slopes of Windham Mountain and minutes drive from ...
From $3429 per night (USD)
VRBO
From $1881 per night (USD)
VRBO
*** Estate Main House***
Bedrooms:
5
Bathrooms:
7
Sleeps:
24
Summary: ***PLEASE DO NOT HIT THE “RESERVE” BUTTON UNTIL YOU CONFIRM VIA EMAIL PRICING & AVAILABILITY. USE ONLY THE “CON ...
From $1881 per night (USD)
VRBO
From $1293 per night (USD)
VRBO
**Your Own Carriage House**
Bedrooms:
3
Bathrooms:
5
Sleeps:
16
Summary: ***PLEASE DO NOT HIT THE “RESERVE” BUTTON UNTIL YOU CONFIRM VIA EMAIL PRICING & AVAILABILITY. USE ONLY THE “CON ...
From $1293 per night (USD)
VRBO
From $1492 per night (USD)
VRBO
***Your Own Estate***
Bedrooms:
8
Bathrooms:
12
Sleeps:
46
Summary: **Please message us prior to booking and talking with your group to confirm pricing and availability** 12 BR, ...
From $1492 per night (USD)
VRBO
From $546 per night (USD)
VRBO
Red Lift Cabin - Close to town, hiking and biking
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Just 2.5 hours from NYC in the heart of the Catskills. One of a kind entirely renovated townhouse. 3 minutes walking dis ...
From $546 per night (USD)
VRBO
From $270 per night (USD)
VRBO
Charming 3 bedroom, 2 bathroom chalet on the mountain!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Well lit, open floor plan, with wood burning fireplace. You'll be staying right on Windham Mountain - so close to skiin ...
From $270 per night (USD)
VRBO
From $270 per night (USD)
Expedia
Ski on and Off Windham Mountain Village Townhome Unit
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This is a townhouse unit located within the Windham Mountain Village Association. It is located at at the base of Windh ...
From $270 per night (USD)
Expedia
From $1080 per night (USD)
VRBO
Ski-in / Ski-out luxury 3-bedroom Windham condo with outdoor pool and hot-tub
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Get ready to relax in this 3-bedroom condo in Windham. With 2 king beds and 2 bunk beds, guests will have plenty of spac ...
From $1080 per night (USD)
VRBO
From $396 per night (USD)
Expedia
Beautiful Windham Chalet 2 minutes to Town and the Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Beautiful Chalet with a host of year-round activities! Close to skiing, snowboarding, sledding, snowshoeing, mountain bi ...
From $396 per night (USD)
Expedia
From $934 per night (USD)
VRBO
BRAND NEW completely renovated house in Windham, 5 bed/ 3 bath
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Welcome to our beautiful, cozy mountain retreat! Our beautiful and spacious home is brand new and completely renovated. ...
From $934 per night (USD)
VRBO
From $374 per night (USD)
Expedia
The Ultimate Windham Getaway With Hot Tub & Sauna
Bedrooms:
2
Bathrooms:
4
Sleeps:
9
Ready for the season, this retreat is perfectly situated in the town of Windham, New York. Whether it’s hike, bike, or s ...
From $374 per night (USD)
Expedia
From $865 per night (USD)
VRBO
Après Chalet|Ski|Luxury|Sauna|HotTub|Firepit|Disco
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
About this space Nestled in the heart of the Catskills, this Windham retreat offers both adventure and serenity, just 5 ...
From $865 per night (USD)
VRBO
From $571 per night (USD)
VRBO
Amazing Location, Steps Away from Magic Carpet to Main Lodge.
Bedrooms:
3
Bathrooms:
3
Sleeps:
10
Welcome to a “Change of Altitude,” an immaculate 3 Bedroom/3 Bath Townhouse that’s a short walk from Windham Main Lodge ...
From $571 per night (USD)
VRBO
From $2808 per night (USD)
VRBO
Spacious Cabin near Hunter & Windham Mountains - 5-25-minute drive - 6 Bedrooms
Bedrooms:
6
Bathrooms:
6
Sleeps:
16
This Windham cabin minutes from Hunter and Windham Mountains, boasts 6 inviting bedrooms, including 1 king bed, 4 queen ...
From $2808 per night (USD)
VRBO
From $276 per night (USD)
Expedia
2 Mi to Windham Mountain: Scenic Home w/ Fire Pit!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Updated Interior w/ Modern Decor & Appliances | Office w/ Dedicated Workspace & Large Windows | Pet Friendly w/ Fee Qui ...
From $276 per night (USD)
Expedia
From $747 per night (USD)
VRBO
In the Heart of Windham - Best Location
Bedrooms:
3
Bathrooms:
5
Sleeps:
13
Discover this 5-bedroom gem in Windham. This pleasant house features 1 king bed and 4 queen beds, perfect for a group ge ...
From $747 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Cozy Mtn-View Chalet < 2 Mi to Windham Slopes
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Private Hot Tub | Scenic Fireside Setting | Easy Access to Windham & Hunter Mountain Skiing There's no shortage of scen ...
From $347 per night (USD)
Expedia
$LUXURIOUS & SERENE SKI-IN/ SKI-OUT \Winterfell\ LODGE$
From $1929 per night (USD)
VRBO
LUXURIOUS & SERENE SKI-IN/ SKI-OUT \"Winterfell\" LODGE
Bedrooms:
6
Bathrooms:
6
Sleeps:
12
Welcome to an unparalleled luxury living experience at this exquisite post-and-beam, charming **Ski-in/ Ski-Out, lodge o ...
From $1929 per night (USD)
VRBO
Click For Pricing
Expedia
Fully updated townhome 200 feet from slopes of Windham Mountain
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
This 3-bedroom 3 bath townhome 200 feet from the Windham ski lift is perfect for your escape. With a king bed, 2 bunk be ...
Click For Pricing
Expedia
From $1295 per night (USD)
VRBO
5-Bedroom Luxury Home on 7 Secluded Acres (10min from Windham Mountain)
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Enjoy a day on the slopes or hiking, followed by a hot tub for sore muscles, wine by the fire, or a movie in the games r ...
From $1295 per night (USD)
VRBO
From $814 per night (USD)
Expedia
September Special! Choose a complimentary fun experience - see details below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
September Special! Farmhouse renters [min. 2 nights] enjoy your choice of one complimentary event in our luxury barn or ...
From $814 per night (USD)
Expedia
From $1278 per night (USD)
VRBO
Ski-in, Ski-out GORGEOUS mountain chalet in prime location
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Beautiful wood and stone chalet directly off a green level ski/summer bike or hike run close to base of Windham mountain ...
From $1278 per night (USD)
VRBO
From $2769 per night (USD)
VRBO
6-bedroom SKI Off Chateau at Windham Mountain Club with WiFi
Bedrooms:
4
Bathrooms:
6
Sleeps:
10
Escape to this superb 6-bedroom Ski Off Chateau at Windham Mountain Club and enjoy Apres-Ski Each room of this Smart ho ...
From $2769 per night (USD)
VRBO
From $608 per night (USD)
VRBO
Spacious 5-bedroom house in marvelous Windham with AC, WiFi & wood burning stove
Bedrooms:
2
Bathrooms:
5
Sleeps:
11
Experience the Catskills at The Quad Six, a spacious 5-bedroom, 2-bathroom vacation home in Windham, NY. Located near bo ...
From $608 per night (USD)
VRBO
From $454 per night (USD)
VRBO
Cozy townhouse steps away from Windham Mountain- zip code 12496
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Note: When making vacation reservations, please plan ahead by including lift tickets in your purchase – advanced purchas ...
From $454 per night (USD)
VRBO
From $1472 per night (USD)
VRBO
Lux Chalet-Ski View. 2 Fireplaces. Pool. Hot Tub. Sauna. 5 min from Windham Ski
Bedrooms:
4
Bathrooms:
4
Sleeps:
12
Black Bear Cabin: Your Luxurious Mountain Retreat Luxury 3,300 sqft Ski and Golf Chalet with 4 bedrooms + 4 ensuite bat ...
From $1472 per night (USD)
VRBO
From $322 per night (USD)
Expedia
Mountain View Ski Minutes to Windham & Hunter
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
At this cozy mountain view cabin, you can wake up minutes from the ski lifts. We are 4 minutes from the ski slopes of Wi ...
From $322 per night (USD)
Expedia
From $267 per night (USD)
VRBO
Ski, Hike & Golf: Pet-Friendly Windham Retreat
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
2 Mi to Windham Mountain Club | Furnished Deck | Peaceful, Wooded Surroundings | Fireplace Surrounded by lush woodlands ...
From $267 per night (USD)
VRBO
From $172 per night (USD)
Expedia
Country Room. Cozy room with a Queen-Size bed, en-suite bathroom, and FREE breakfast. Sleeps 2.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You're booking the smallest room at Mountain Treasure Bed and Breakfast. Other amenities in this room include: -QUEEN S ...
From $172 per night (USD)
Expedia
From $195 per night (USD)
VRBO
Fiddler On The Roof Room Room with mountain views, a King-Size bed, en suite bathroom, and FREE breakfast. It sleeps 2.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You're booking one room at Mountain Treasure Bed and Breakfast. Other amenities in this room include: -KING Size Bed -Pr ...
From $195 per night (USD)
VRBO
From $205 per night (USD)
Expedia
Americana Room. Elegant room with a King-Size bed, en suite bathroom, and mountain views. Sleeps 2. A gourmet breakfast is FREE and served fresh each morning. Americana Room is located on the second floor of Mountain Treasure Bed and Breakfast
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You're booking one room at Mountain Treasure Bed and Breakfast. Other amenities in this room include: -KING Size Bed wit ...
From $205 per night (USD)
Expedia
From $172 per night (USD)
VRBO
Art Nouveau Room Large room decorated in the Art Nouveau style with FULL-size bed, en suite bathroom.FREE breakfast. Sleeps 2.
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
You're booking one room at Mountain Treasure Bed and Breakfast. Other AMENITIES in this room include: -FULL-Size Bed wit ...
From $172 per night (USD)
VRBO
From $792 per night (USD)
VRBO
Cozy Lux Mountain Lodge-Hot Tub-Mountain Views-10min to Skiing-Windham Hunter
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
KEY FEATURES: • Sleeps 10 with 4 queen beds and 1 king bed • Views, Views, Views! Our home, at the end of a cul-de-sac, ...
From $792 per night (USD)
VRBO
From $1012 per night (USD)
VRBO
Luxe Party Retreat: Theater/Karaoke/Games/Hot tub/swimming pool
Bedrooms:
2
Bathrooms:
5
Sleeps:
16
An Experience Tailored for You Private Cinema and Entertainment Our home theater is equipped with a 4K RGB laser proje ...
From $1012 per night (USD)
VRBO
From $814 per night (USD)
Expedia
September Special! Choose a complimentary fun experience - see details below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
September Special! Farmhouse renters [min. 2 nights] enjoy your choice of one complimentary event in our luxury barn or ...
From $814 per night (USD)
Expedia
From $540 per night (USD)
VRBO
Mountain Chalet with Hot Tub, Ski, & Amazing Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
*New Listing Discount applied to all bookings made before 5/30/25!!* Chalet retreat in Hensonville, nestled convenientl ...
From $540 per night (USD)
VRBO
From $405 per night (USD)
VRBO
Sauna, Mnt Views, Hot tub, <2 mins to slopes
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
You'll love our Ski house for your trip to Windham Mountain! Here's why: - Centrally located to 2 mins from the village ...
From $405 per night (USD)
VRBO
From $308 per night (USD)
VRBO
All-Season Condo - Ski Windham l Hunter l Pool l Hike l Fish
Bedrooms:
2
Bathrooms:
2
Sleeps:
8
Unwind in this serene, inviting condo, a haven for year-round relaxation. Experience the natural splendor of the Catskil ...
From $308 per night (USD)
VRBO
Click For Pricing
Expedia
Walk to Ski Lift: Family-Friendly Windham Townhome
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Private Hot Tub | Pets Welcome w/ Fee | Near Hiking & Biking Experience the Catskills' year-round natural beauty at thi ...
Click For Pricing
Expedia
From $693 per night (USD)
VRBO
Valley VIEWS! Hot tub, Game Room, Acres to Roam!
Bedrooms:
3
Bathrooms:
4
Sleeps:
13
Escape to this luxurious country home, nestled on 10 private acres with breathtaking views of the Durham Valley and the ...
From $693 per night (USD)
VRBO
From $789 per night (USD)
Expedia
Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests,...
Bedrooms:
3
Bathrooms:
6
Sleeps:
12
Wonderful in Windham Hudson Valley Mountain Retreat, secluded, surrounded by beautiful forests, ample outdoor seating, ...
From $789 per night (USD)
Expedia
From $937 per night (USD)
VRBO
Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out,...
Bedrooms:
3
Bathrooms:
5
Sleeps:
12
Windham Mountainside Marvel Contemporary Renovated Retreat with Mountain Views, Ski-In/Ski-Out, Spacious Living Spaces ...
From $937 per night (USD)
VRBO
From $814 per night (USD)
Expedia
September Special! Choose a complimentary fun experience - see details below!
Bedrooms:
4
Bathrooms:
4
Sleeps:
8
September Special! Farmhouse renters [min. 2 nights] enjoy your choice of one complimentary event in our luxury barn or ...
From $814 per night (USD)
Expedia
From $844 per night (USD)
VRBO
Spacious 7-bedroom house with AC, WiFi in peaceful Hensonville
Bedrooms:
6
Bathrooms:
7
Sleeps:
16
Get ready to relax in this marvelous 7-bedroom house in Hensonville. With 2 king beds, 3 queen beds, 1 full bed, and 2 t ...
From $844 per night (USD)
VRBO
From $7018 per night (USD)
Expedia
Spacious 5-bedroom house in charming Windham centrally located in town.
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Windham is waiting for you at this 5-bedroom house. This beautiful property features 4 queen beds and 1 king bed, perfec ...
From $7018 per night (USD)
Expedia
From $258 per night (USD)
VRBO
Delightful 3-bedroom chalet with WiFi in Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
This fabulous chalet in Windham offers a cozy retreat for guests. With 3 bedrooms including a queen, twin, and bunk bed, ...
From $258 per night (USD)
VRBO
From $459 per night (USD)
Expedia
Idyllic Mountain Stay Hot Tub, Wood Stove, Games
Bedrooms:
3
Bathrooms:
5
Sleeps:
14
Escape to this stylish mountain retreat, situated on 3 private acres with breathtaking views of Windham + Hunter Mountai ...
From $459 per night (USD)
Expedia
From $448 per night (USD)
VRBO
3-bedroom All-Season condo at Enclave in amazing Windham ON MOUNTAIN
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Discover this marvelous 3-bedroom gem in Windham. This delightful condo features 2 king beds and 2 sets of bunk beds, pe ...
From $448 per night (USD)
VRBO
From $1146 per night (USD)
VRBO
Entire lodge in Windham, New York on 12 acres and bordering a state park
Bedrooms:
4
Bathrooms:
5
Sleeps:
16
Discover the charm of Windham, NY, a four-season retreat in the Catskill Mountains, just two hours from NYC! Mt. Pisgah ...
From $1146 per night (USD)
VRBO
From $891 per night (USD)
VRBO
Brand NEW MINT Windham 5BR/4.5BA home on 5 acre, wooded hilltop.
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
MINT 5BR, 4.5BA, brand new home. Full modern furnishing complete 5/1. Panoramic views from 5 acre hilltop with forest ba ...
From $891 per night (USD)
VRBO
From $508 per night (USD)
VRBO
Serene Catskills Riverfront Chalet. HotTub + Views!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Serene mountain retreat where nature meets comfort. Set on 3 private acres with a river running through and direct acces ...
From $508 per night (USD)
VRBO
From $404 per night (USD)
VRBO
Charming 3-bedroom farmhouse with hot tub in the Catskills
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Escape to this serene 3-bedroom, 2-bathroom home nestled in the heart of Windham, NY! Perfect for a relaxing family geta ...
From $404 per night (USD)
VRBO
From $631 per night (USD)
Expedia
Drift Haus|4.5BR+ Mountain Lodge Room only
Bedrooms:
3
Bathrooms:
4
Sleeps:
14
Escape the ordinary at this spacious alpine lodge in the heart of Windham. Tucked into a quiet wooded setting, this five ...
From $631 per night (USD)
Expedia
From $266 per night (USD)
VRBO
Stylish 3BR Getaway – 3 Minutes to Windham Mountain Resort, AC & WiFi Included!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Located in Windham, enjoy what this 3-bedroom house has to offer. With 2 king beds and 1 full bed, guests can relax in t ...
From $266 per night (USD)
VRBO
From $348 per night (USD)
Expedia
2 Min Walk to Windham Town | Hot Tub | Fire Pit
Bedrooms:
2
Bathrooms:
4
Sleeps:
11
Escape to Windham in this beautifully designed, pet-friendly home—just a 2-minute walk to the village’s charming shops, ...
From $348 per night (USD)
Expedia
From $217 per night (USD)
VRBO
5 State View-Cozy Mountain Loft
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Your Acra adventure begins at this delightful cabin. This cozy retreat features 1 bedroom with a king bed and bunk bed, ...
From $217 per night (USD)
VRBO
From $195 per night (USD)
VRBO
1850's Bungalow With A View!
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Welcome to our 1850's Bungalow with a stunning view over 5 states. This charming retreat features two cozy bedrooms, an ...
From $195 per night (USD)
VRBO
From $350 per night (USD)
VRBO
Ski, Hike & More: Year-Round Gem in Windham
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Walk to Main Street Shops & Restaurants | Amazing Bird Watching | Secluded Deck w/ Grill Escape to the mountains at thi ...
From $350 per night (USD)
VRBO
From $456 per night (USD)
Expedia
MIRROR CABIN IN THE FOREST WITH HOT TUB
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Mirror Cabin Retreat | Modern Luxury in the Catskills Discover the ultimate Catskills getaway at this one-of-a-kind mir ...
From $456 per night (USD)
Expedia
From $231 per night (USD)
VRBO
Whispering River - Catskills New York
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
Welcome to the newly renovated house with central Heating and Cooling located just minutes from skiing, hiking and every ...
From $231 per night (USD)
VRBO
From $670 per night (USD)
VRBO
THE PAINTED COW- 5 acre farm, walk to Mainstreet, 1 mile to slopes in Windham!!
Bedrooms:
3
Bathrooms:
6
Sleeps:
14
Highest-rated superhost Airbnb- new to VRBO! Escape to Nature in All Four Seasons at this beautifully renovated 1900s f ...
From $670 per night (USD)
VRBO
From $1620 per night (USD)
VRBO
Family-Friendly Windham Estate, Swimming Pond, Spa
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Summary: Escape to the ultimate Catskills retreat at The Mountain House! This 8-BR, 6.5-BA home on 10.5 acres features a ...
From $1620 per night (USD)
VRBO
From $476 per night (USD)
Expedia
Modern A-Frame Cabin 3BR + Loft Luxury Retreat in Windham, NY
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Discover year-round comfort and style at this beautifully designed A-frame cabin just 5 minutes from Windham Mountain an ...
From $476 per night (USD)
Expedia
From $340 per night (USD)
VRBO
4-bedroom country house in serene Windham with WiFi, AC
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
This 4-bedroom Center Hall Colonial is perfect for your escape to Windham. With 1 king bed and 3 queen beds, this wonder ...
From $340 per night (USD)
VRBO
Click For Pricing
Expedia
Peaceful 3-BR Getaway Just Outside Windham Town
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Summary: Set within Windham’s sought-after Windmont community, this expansive mountain retreat offers privacy, comfort, ...
Click For Pricing
Expedia
From $810 per night (USD)
VRBO
Woodside Cabin #2 on Lake Heloise
Bedrooms:
1
Bathrooms:
1
Sleeps:
18
Charming cabin to stay and play in at the lake. Have fun swimming and fishing on the lake. This property was a campsite ...
From $810 per night (USD)
VRBO
From $314 per night (USD)
Expedia
Tiny Cabin #1 by Windham NY Escape 'Catskill Gem'
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Nestled in the Catskills, Cabin 1 at Windham Escape is a cozy 500 sq ft retreat with rustic charm and modern comforts. I ...
From $314 per night (USD)
Expedia
From $314 per night (USD)
VRBO
Tiny Cabin #2 by Windham NY Escape 'Cozy Stay'
Bedrooms:
1
Bathrooms:
2
Sleeps:
7
Tiny Cabin Cabin 2 offers the perfect mix of mountain tranquility and cozy comfort. With 500 sq ft of thoughtfully arran ...
From $314 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Tiny Cabin #3 by Windham NY Escape 'Forest View'
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Escape the noise in Tiny Cabin 3, a cozy 500 sq ft retreat surrounded by woods and wildlife. It comfortably accommodates ...
From $282 per night (USD)
Expedia
From $282 per night (USD)
VRBO
Tiny Cabin #4 by Windham NY Escape 'Cabin Comfort'
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Tiny Cabin 4 is a peaceful retreat in the Catskills, where forest views and the gentle sounds of nearby Batavia Kill cre ...
From $282 per night (USD)
VRBO
From $282 per night (USD)
Expedia
Tiny Cabin #5 by Windham NY Escape 'Scenic Stay'
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Relax in Tiny Cabin 5, nestled on a peaceful hillside with tranquil forest views. This 500 sq ft cabin comfortably sleep ...
From $282 per night (USD)
Expedia
From $1411 per night (USD)
VRBO
The Summit House - Private Upstate Estate with Unmatched Mountain Views
Bedrooms:
5
Bathrooms:
6
Sleeps:
14
One of a kind masterpiece perched above the clouds outside Windham. Experience complete privacy at this stunning all-s ...
From $1411 per night (USD)
VRBO
From $542 per night (USD)
Expedia
This chalet is a 4 bedroom(s), 2 bathrooms, located in Hensonville, NY.
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
Chalet in Hensonville, NY · ★★★★ ★ · 4 BR · 6 Beds · 2 Baths Welcome to Mountain View Chalet, a peaceful Catskills esca ...
From $542 per night (USD)
Expedia
From $454 per night (USD)
VRBO
This chalet is a 4 bedroom(s), 3 bathrooms, located in Hensonville, NY.
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
Chalet in Hensonville · ★★★★★ · 4 BR · 12 Beds · 3 Baths Welcome to Windham Pine Chalet, a cozy yet elegant chalet nest ...
From $454 per night (USD)
VRBO
From $347 per night (USD)
Expedia
Fabulous house with AC in charming Windham-located right by Windham Mountain
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Located in Windham, this house is a dream. With 4 bathrooms equipped with amenities like a bathtub and hair dryer, guest ...
From $347 per night (USD)
Expedia
From $1000 per night (USD)
VRBO
Fireplaces, Home Theater, Ski-In/Out Windham Lodge
Bedrooms:
6
Bathrooms:
8
Sleeps:
16
Unwind at Wanderwood Lodge, an 8BR retreat with ski-in/ski-out access on Windham Mountain. Cozy up by wood-burning firep ...
From $1000 per night (USD)
VRBO
From $324 per night (USD)
Expedia
3 Mi to Windham Mountain: Private Hilltop Retreat
Bedrooms:
3
Bathrooms:
4
Sleeps:
9
Stunning Views of Winter Slopes | Hot Tub | Playroom Shed for Kids Plan a mountain getaway the whole family will love — ...
From $324 per night (USD)
Expedia
From $279 per night (USD)
VRBO
Secluded Retreat w Hot Tub in Windham
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Summary: Escape to this secluded Catskills retreat! Just minutes from Windham Mountain, Hunter, hiking trails, and lakes ...
From $279 per night (USD)
VRBO
From $755 per night (USD)
Expedia
Unwind Windham, Chalet
Bedrooms:
3
Bathrooms:
4
Sleeps:
6
Tucked away in the heart of the Catskills, Unwind Windham is more than just a place to stay—it’s a retreat designed for ...
From $755 per night (USD)
Expedia

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Results: 298 Rentals